(S)-4-Hydroxymethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

Base Information

Chemical Name:(S)-4-Hydroxymethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester
CAS No.:418812-75-6
Molecular Formula:C₁₅H₂₅NO₆
Molecular Weight:315.367
Hs Code.:

Synonyms:(S)-4-Hydroxymethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

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Chemical Property of (S)-4-Hydroxymethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

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Technology Process of (S)-4-Hydroxymethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

There total 1 articles about (S)-4-Hydroxymethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 91229-91-3
tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate

: 418812-75-6
(S)-4-Hydroxymethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 88 percent / 1,2-dimethoxy-ethane / 75 °C

2: HCl / methanol; H₂O / pH 3.5 - 4.0

3: NaBH₃CN / 4 h

With hydrogenchloride; sodium cyanoborohydride; In methanol; 1,2-dimethoxyethane; water;
DOI:10.1021/ol0255458

Reference yield: 12.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 418812-75-6
(S)-4-Hydroxymethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

: 163190-43-0
tert-Butyl (2S,4S)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylpyroglutamate

: 163190-48-5
tert-Butyl (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldiphenylsilyloxymethylpyroglutamate

Guidance literature:: With dmap; triethylamine; In dichloromethane; 1.) 0 deg C, 15 min, 2.) 2 days;
DOI:10.1039/P19960001131

Reference yield:

: 418812-75-6
(S)-4-Hydroxymethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

: (S)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-3-[1,2]dithiolan-4-yl-propionic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 95 percent / LiOH / tetrahydrofuran; H₂O / 0 °C

2: NMM / tetrahydrofuran / -15 °C

3: NaBH₄ / tetrahydrofuran / 0 °C

4: 93.8 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

5: 91.1 percent / dimethylformamide / 1.5 h / 20 °C

6: 99 percent / NaOH / ethanol; H₂O / 1 h / 0 °C

7: 98 percent / I₂; NaOAc / CHCl₃; H₂O / 0 °C

8: 69 percent / HCl / ethyl acetate; H₂O / 4 h / 20 °C

9: 78.8 percent / HOBt; EDC; Et₃N / dimethylformamide / 18 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; iodine; sodium acetate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ol0255458